Issue 4, 2016

N-Heterocyclic carbene-catalyzed [4 + 2] cyclization of α,β-unsaturated carboxylic acids bearing γ-H with isatins: an enantioselective synthesis of spirocyclic oxindole–dihydropyranones

Abstract

An NHC-catalyzed asymmetric [4 + 2] annulation of isatins and α,β-unsaturated carboxylic acids bearing γ-H gave spirocyclic oxindole–dihydropyranones successfully via an in situ activation strategy. This protocol featured easy availability of raw materials, good yields and excellent enantioselectivities (up to 99% ee).

Graphical abstract: N-Heterocyclic carbene-catalyzed [4 + 2] cyclization of α,β-unsaturated carboxylic acids bearing γ-H with isatins: an enantioselective synthesis of spirocyclic oxindole–dihydropyranones

Supplementary files

Article information

Article type
Paper
Submitted
19 Oct 2015
Accepted
16 Dec 2015
First published
16 Dec 2015

Org. Biomol. Chem., 2016,14, 1485-1491

Author version available

N-Heterocyclic carbene-catalyzed [4 + 2] cyclization of α,β-unsaturated carboxylic acids bearing γ-H with isatins: an enantioselective synthesis of spirocyclic oxindole–dihydropyranones

L. Zhu, C. Yu, T. Li, Y. Wang, Y. Lu, W. Wang and C. Yao, Org. Biomol. Chem., 2016, 14, 1485 DOI: 10.1039/C5OB02160J

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